Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s)

Tony K.M. Shing; Wai F. Wong; Hau M. Cheng; Wun S. Kwok; King H. So

doi:10.1021/ol062873p

Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s)

Tony K.M. Shing, Wai F. Wong, Hau M. Cheng, Wun S. Kwok, King H. So

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

49 Citations (Scopus)

Abstract

(Chemical Equation Presented) Intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.

Original language	English
Pages (from-to)	753-756
Number of pages	4
Journal	Organic Letters
Volume	9
Issue number	5
DOIs	https://doi.org/10.1021/ol062873p
Publication status	Published - 2007 Mar 1

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol062873p

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abstract = "(Chemical Equation Presented) Intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.",

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AU - Shing, Tony K.M.

AU - Wong, Wai F.

AU - Cheng, Hau M.

AU - Kwok, Wun S.

AU - So, King H.

PY - 2007/3/1

Y1 - 2007/3/1

N2 - (Chemical Equation Presented) Intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.

AB - (Chemical Equation Presented) Intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar derivatives with one to four free hydroxyl group(s) is reported. The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields. This new methodology alleviates protection/deprotection steps and makes the synthetic route shorter and more efficient.

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Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s)

Abstract

ASJC Scopus subject areas

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